Triphenylene compounds, method of manufacturing the same and organic electroluminescent devices employing the same

a technology of triphenylene compounds and organic electroluminescent devices, which is applied in the direction of discharge tube luminescnet screens, natural mineral layered products, etc., can solve the problems of high driving voltage, unknown triphenylene compounds having a silylethyl group, and limited compounds which can be employed, etc., to achieve high excited triplet energy, high heat and light resistance, and high processability

Inactive Publication Date: 2011-09-27
GUNMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

Under these circumstances, it is an object of the present invention to provide a novel triphenylene compound having a high level of excited triplet energy and containing a silylethynyl group, a method of manufacturing the same and a novel phosphorescent device made by employing the same in its luminous layer and capable of being driven by a low voltage.
The compound of the present invention is stable because of its high heat and light resistance and is high in processability because of its solubility in an organic solvent. The compound of the present invention is useful as an optical material for an organic electroluminescent device or the like owing to its property of emitting fluorescence and phosphorescence.
Moreover, those of the compounds of the present invention which emit phosphorescence are suitable as a host compound in the luminous layer of a phosphorescent device owing to its high excited triplet energy and make it possible to produce a novel phosphorescent device.

Problems solved by technology

The host compound is required to have a higher level of excited triplet state energy than that of the phosphorescent dopant, and the compounds which can be employed are, therefore, limited.
However, it is considered necessary to develop a novel host compound, since the phosphorescent devices employing the existing phosphorescent host compounds have drawbacks including the necessity for a high driving voltage.
However, there has not been known any triphenylene compound having a silylethynyl group.
Attempts have been made to isolate a triphenylene compound (terminating at H) having a silylethynyl group by the desilylation reaction of 2,3,6,7,10,11-hexakis(trimethylsilylethynyl)triphenylene, but its isolation has been difficult, as it is unstable in the air and immediately undergoes a polymerization reaction to form a polymeric product.

Method used

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  • Triphenylene compounds, method of manufacturing the same and organic electroluminescent devices employing the same
  • Triphenylene compounds, method of manufacturing the same and organic electroluminescent devices employing the same
  • Triphenylene compounds, method of manufacturing the same and organic electroluminescent devices employing the same

Examples

Experimental program
Comparison scheme
Effect test

example 1

1. Synthesis of 2,3,6,7,10,11-Hexakis(trimethylsilylethynyl)triphenylene—General Formula (V)

The synthesis of 2,3,6,7,10,11-hexakis(trimethylsilylethynyl)triphenylene was performed by the method as described below.

1.1. Synthesis of Triphenylene

Triphenylene was synthesized by the reaction shown below:

(Materials and Amounts Employed)

2-Bromofluorobenzene (Tokyo Kasei, 99%): 10.12 g / 5.73×10-z mole

Mg (Wako, flaky, 99.5%): 1.54 g / 6.30×10−2 mole

THF (treated with benzophenoneketyl): 85+15 ml

(Operation and Results)

A 200-ml three-necked flask having a dropping funnel, a Dimroth condenser and a spinner was subjected to flameout treatment and purged with argon. The flask was charged with Mg and it was subjected to two hours of activation at 180° C. The flask was charged with 85 ml of THF, and the dropping funnel with 2-bromofluorobenzene and 15 ml of THF, and their dropping took 20 minutes (the generation of heat started immediately after the dropping was started). The dropping was followed by s...

example 2

Synthesis and Spectral Analysis of 2,3,6,7,10,11-Hexakis(triisopropylsilylethynyl)triphenylene

Triisopropylsilylacetylene was first synthesized by the reaction shown below:

This was reacted with 2,3,6,7,10,11-hexabromotriphenylene to synthesize 2,3,6,7,10,11-hexakis(triisopropylsilylethynyl)triphenylene (general formula (VI)). The reaction was similar to that employed for 2,3,6,7,10,11-hexakis-(trimethylsilylethynyl)triphenylene. The yield was 55%.

The ultraviolet-visible absorption spectra of 2,3,6,7,10,11-hexakis-(triisopropylsilylethynyl)triphenylene were determined in hexane at room temperature. The results are shown in FIG. 10 with data on triphenylene and 2,3,6,7,10,11-hexakis(trimethylsilylethynyl)triphenylene.

A shift to a longer wavelength was observed with 2,3,6,7,10,11-hexakis(triisopropylsilylethynyl)triphenylene, too, as compared with triphenylene.

The fluorescence spectra of 2,3,6,7,10,11-hexakis (triisopropyl-silylethynyl)triphenylene were determined in 3-methylpentane (3-...

example 3

Manufacture of a Phosphorescent Device Including 2,3,6,7,10,11-hexakis-(trimethylsilylethynyl)triphenylene (Compound 1) as a Host Compound and Confirmation of Emission

A transparent supporting substrate was prepared by forming a layer of ITO having a thickness of 150 nm on a glass substrate by vapor deposition. The transparent supporting substrate was fixed to a substrate holder in an evaporator, and the evaporator was furnished with an evaporation boat of molybdenum containing copper phthalocyanine (hereinafter expressed by symbol CuPc), an evaporation boat of molybdenum containing NPD, an evaporation boat of molybdenum containing Ir(ppy)3, an evaporation boat of molybdenum containing Compound 1, an evaporation boat of molybdenum containing BCP, an evaporation boat of molybdenum containing Alq3, an evaporation boat of molybdenum containing lithium fluoride and an evaporation boat of tungsten containing aluminum.

A vacuum tank had its pressure reduced to 1×10−3 Pa, the evaporation boa...

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Abstract

The present invention provides a novel compound represented by general formula (I) below, a method of manufacturing the same and an organic electroluminescent device employing the same:where R1 to R6 are independent of one another and are each a hydrogen atom or a substituent represented by general formula (II) below, and at least one of R1 to R6 is a substituent represented by general formula (II):—C≡C—SiRaRbRc  (II)where Ra, Rb and Rc are independent of one another and are each an aliphatic hydrocarbon group having 1 to 10 carbon atoms or an aromatic hydrocarbon group.

Description

TECHNICAL FIELDThe present invention relates to a novel triphenylene compound having a high level of excited triplet energy and containing a silylethynyl group, a method of manufacturing the same and an organic electroluminescent device employing the same.BACKGROUND ARTThere is already known an organic electroluminescent device having a multilayer laminated structure and employing phosphorescence (an organic electroluminescent device employing phosphorescence being hereinafter referred to also as a phosphorescent device) (see U.S. Pat. No. 6,097,147). A device relying solely on fluorescence for emission of light has a theoretical limit of 25% as its internal quantum efficiency, since it employs an excited singlet state, but a phosphorescent device is considered to have a theoretical limit of 100% as its internal quantum efficiency, since excited energy of the triplet state contributes to emission of light. Accordingly, a phosphorescent device is superior to a fluorescent device, as ...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): H01L51/54C09K11/06
CPCC07F7/0809C09K11/06H01L51/0054H01L51/0094C09K2211/1011H01L51/0076H01L51/0085H01L51/5016C07F7/0805Y10S428/917H10K85/622H10K85/731H10K85/342H10K85/40H10K50/11H10K2101/10
Inventor MATSUMOTO, HIDEYUKIKYUSHIN, SOICHIRONEGISHI, KEISUKEONO, YOUHEIUCHIDA, MANABUOOMORI, HIDEFUMI
Owner GUNMA UNIVERSITY
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